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Pauson−Khand Reaction of Optically Active 6,7-Bis(tert-butyldimethylsiloxy)non-1-en-8-ynes

Authors :
Chisato Mukai
Jin Sung Kim
Miyoji Hanaoka
Hiroshi Sonobe
Source :
The Journal of Organic Chemistry. 65:6654-6659
Publication Year :
2000
Publisher :
American Chemical Society (ACS), 2000.

Abstract

Treatment of (6S,7S)-7-bis(tert-butyldimethylsiloxy)non-1-en-8-ynes with dicobalt octacarbonyl gave the corresponding cobalt complex. This complex was subsequently exposed to the Pauson-Khand conditions in the presence of a promoter such as cyclohexylamine, thioanisole, methyl isopropyl sulfide, and butyl methyl sulfide ending up with the stereoselective production of the (2S,3S,6S,7S)-7-methylbicyclo[4.3.0]nonenone derivatives instead of the expected (2S,3S,7S)-bicyclo[5.3.0]decenone species.

Details

ISSN :
15206904 and 00223263
Volume :
65
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....62251d565b6deaf8227fc60e40b79377
Full Text :
https://doi.org/10.1021/jo0008082